8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2,4-dideoxy-3-O-(4-methoxybenzyl)-β-D-xylopyranoside

Base Information

• Chemical Name: 8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2,4-dideoxy-3-O-(4-methoxybenzyl)-β-D-xylopyranoside
• CAS No.: 180335-98-2
• Molecular Formula: C₃₃H₄₇NO₈
• Molecular Weight: 585.738

Synonyms:8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2,4-dideoxy-3-O-(4-methoxybenzyl)-β-D-xylopyranoside

Chemical Property of 8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2,4-dideoxy-3-O-(4-methoxybenzyl)-β-D-xylopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2,4-dideoxy-3-O-(4-methoxybenzyl)-β-D-xylopyranoside

There total 5 articles about 8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2,4-dideoxy-3-O-(4-methoxybenzyl)-β-D-xylopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(4-methoxybenzyl)-4-O-(methylthio)thiocarbonyl-β-D-glucopyranoside (180335-96-0) → 8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2,4-dideoxy-3-O-(4-methoxybenzyl)-β-D-xylopyranoside (180335-98-2)

Guidance literature:

With azobisisobutyronitrile; tri-n-butyl-tin hydride; In toluene; at 80 ℃; for 2h;

DOI:10.1016/0008-6215(96)00047-X

Reference yield:

ω-methoxycarbonyloctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (71048-95-8) → 8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2,4-dideoxy-3-O-(4-methoxybenzyl)-β-D-xylopyranoside (180335-98-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / dimethylformamide / 0.5 h / -50 - -40 °C

1.2: 68 percent / dimethylformamide / 1 h / -50 - 20 °C

2.1: 83 percent / HCl; sodium cyanoborohydride; 3 Angstroem molecular sieves / diethyl ether; tetrahydrofuran / 0.67 h / 0 °C

3.1: 73 percent / 4-dimethylaminopyridine / acetonitrile / 22 h / 20 °C / Heating

4.1: 90 percent / α,α'-azobisisobutyronitrile; tributyltin hydride / toluene / 2 h / 80 °C

With hydrogenchloride; dmap; 3 A molecular sieve; azobisisobutyronitrile; tri-n-butyl-tin hydride; sodium hydride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Metallation / 1.2: benzylation / 2.1: Ring cleavage / 3.1: Esterification / 4.1: Reduction;

DOI:10.1016/0008-6215(96)00047-X

Reference yield:

p-methoxybenzyl chloride (824-94-2) → 8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2,4-dideoxy-3-O-(4-methoxybenzyl)-β-D-xylopyranoside (180335-98-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / dimethylformamide / 0.5 h / -50 - -40 °C

1.2: 68 percent / dimethylformamide / 1 h / -50 - 20 °C

2.1: 83 percent / HCl; sodium cyanoborohydride; 3 Angstroem molecular sieves / diethyl ether; tetrahydrofuran / 0.67 h / 0 °C

3.1: 73 percent / 4-dimethylaminopyridine / acetonitrile / 22 h / 20 °C / Heating

4.1: 90 percent / α,α'-azobisisobutyronitrile; tributyltin hydride / toluene / 2 h / 80 °C

With hydrogenchloride; dmap; 3 A molecular sieve; azobisisobutyronitrile; tri-n-butyl-tin hydride; sodium hydride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Metallation / 1.2: benzylation / 2.1: Ring cleavage / 3.1: Esterification / 4.1: Reduction;

DOI:10.1016/0008-6215(96)00047-X

upstream raw materials:

8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(4-methoxybenzyl)-4-O-(methylthio)thiocarbonyl-β-D-glucopyranoside

ω-methoxycarbonyloctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

p-methoxybenzyl chloride

8-methoxycarbonyloctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(4-methoxybenzyl)-β-D-glucopyranoside

Downstream raw materials:

8-methoxycarbonyloctyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside

8-methoxycarbonyloctyl 3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside

8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2,4-dideoxy-β-D-xylopyranoside

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